Formamide → 4-Methoxyisoindoline-1,3-dione

HRID 334955

Reaction equation

HRID 334955 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([O:8][C:9](=O)[C:4]=12)=[O:7].C([NH2:16])=O>O>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([NH:16][C:9](=[O:8])[C:4]=12)=[O:7]

Participants

4

Reactant 2

HCID 713FormamideHCID 2911934-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

Product 1

HCID 166382284-Methoxyisoindoline-1,3-dioneYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-methoxyphthalic anhydride (24.0 g, 134.8 mmol) and formamide (120 ml) was stirred and held at 210° C. for 5 hours and was then allowed to cool to room temperature overnight. Water (100 ml) was added and the solid material filtered off under reduced pressure. The crude product was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 3-methoxyphthalimide (8.95 g, 37%) as an off-white solid. 1H NMR (DMSO-d6) 11.08 (1H, br s), 7.78 (1H, dd), 7.45 (1H, d), 7.36 (1H, d), 3.93 (3H, s). MS: [M+H]+ 178.

Workup

  1. filtrationthe solid material filtered off under reduced pressure
  2. washThe crude product was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml)
  3. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-cc793aa1c1a246b88f542acc0c9cf1b0
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Linked notes

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